1-Azido-4-methoxybenzene → 5-(3,4-Dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amine

HRID 1639704Notes

Reaction equation

HRID 1639704 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21]#[N:22])[CH:16]=[CH:17][C:18]=1[Cl:19].C[O-].[Na+]>C(O)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[N:3]=[N:2][N:1]([C:4]3[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)[C:21]=2[NH2:22])[CH:16]=[CH:17][C:18]=1[Cl:19]

Participants

5

Reactant 3

HCID 750041-Azido-4-methoxybenzeneHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 252161605-(3,4-Dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amineYield 34.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred and ice-cooled solution of 1-azido-4-methoxy-benzene (2.000 g, 13.4090 mmol) and 3,4-dichlorophenylacetonitrile (2.994 g, 16.0909 mmol) in absolute ethanol (30 ml), an ice-cooled solution of sodium methoxide (1.087 g, 20.1136 mmol) in absolute ethanol (20 ml) is added drop-wise. The resulting reaction mixture is evaporated and the residue is dissolved in methylene chloride and washed with water, brine, dried over MgSO4, filtered and evaporated to afford ˜4.5 g of crude material as brownish solid. This material is purified by crystallization from methylene chloride and petroleum ether, to obtain the title compound as reddish solid (1.536 g, 34% yield). M.p. 189.9-191.3° C. LC-ESI-HRMS of [M+H]+ shows 335.0483 Da. Calc. 335.046642 Da, dev. 4.9 ppm.

Workup

  1. additionis added drop-wise
  2. customThe resulting reaction mixture
  3. customis evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford ˜4.5 g of crude material as brownish solid
  10. customThis material is purified by crystallization from methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-f968cd1bda7a46fab7d75def5f0912cc
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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